Reacción #3267

Ecuación de reacción

Ethyl acetate

potassium carbonate

aldehyde

4-Methylamino-2-methylsulfanyl-pyrimidine-5-carboxaldehyde

2,6-dichlorophenylacetonitrile

dimethylformamide

→

6-(2,6-dichlorophenyl)-8-methyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-ylideneamine

Rendimiento 40.0%

Disolventes

methylene chloride

—

Petroleum ether

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture was heated
2. 2
   Filtraciónthe solids were filtered
3. 3
   Lavadowashed with ethyl acetate
4. 4
   ConcentraciónThe filtrate was concentrated under reduced pressure
5. 5
   OtroThe residual gum was triturated with 10 mL of water
6. 6
   Filtraciónthe resulting solid was filtered
7. 7
   Lavadowashed well with water
8. 8
   Otrodried
9. 9
   OtroThis crude material was chromatographed
10. 10
    LavadoThe column was eluted with 1:1 (v/v) hexane
11. 11
    Otroethyl acetate, collecting the fractions that
12. 12
    OtroEvaporation of the solvents
13. 13
    Otrogave a solid
14. 14
    Filtraciónthe crystals were filtered

Procedimiento

Powdered potassium carbonate (0.8 g; 5.8 mmol) was added to a solution of 0.220 g (1.2 mmol) of the aldehyde from Example 18 and 0.235 g (1.26 mmol) (ca. 5% excess) of 2,6-dichlorophenylacetonitrile in 2.0 mL of dimethylformamide. The mixture was heated with stirring at 125° C. for 6 hours. Ethyl acetate (5 mL) was added to the cooled mixture, and the solids were filtered and washed with ethyl acetate. The filtrate was concentrated under reduced pressure. The residual gum was triturated with 10 mL of water, and the resulting solid was filtered, washed well with water, and dried. This crude material was chromatographed by placing a chloroform solution on a silica gel column wet with chloroform. The column was eluted with 1:1 (v/v) hexane:ethyl acetate, collecting the fractions that contain the Rf 0.25 spot on tlc (1:1 hexane:ethyl acetate). Evaporation of the solvents gave a solid. The solid product was dissolved in about 0.5 mL of methylene chloride. Crystals develop. Petroleum ether (ca. 2 mL) was added, and the crystals were filtered to provide 0.168 g (40%) of 6-(2,6-dichlorophenyl)-8-methyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-ylideneamine, mp 198°-200° C.

Fuente